Triethylamine → alpha-[[(2,3-Dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol

HRID 486371Notes

Reaction equation

HRID 486371 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([OH:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.[CH3:16][O:17][C:18]1[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=O.C(N(CC)CC)C.[BH4-].[Na+]>CO>[CH3:16][O:17][C:18]1[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][NH:2][CH2:3][CH:4]([OH:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 665812,3-DimethoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 128889092-Amino-1-(3,4-dimethoxyphenyl)ethan-1-ol hydrochloride

Product 1

HCID 14719553alpha-[[(2,3-Dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcoholYield 75.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

α-Aminomethyl-3,4-dimethoxybenzyl alcohol hydrochloride (5.84 g, 25 mmol) was suspended in methanol (30 ml). 2,3-Dimethoxybenzaldehyde (5 g, 30 mmol) was added to the suspension and then triethylamine (3.83 ml, 27.5 mmol) was added dropwise thereto under stirring at room temperature. The resultant solution was heated under reflux for 30 minutes and then sodium borohydride (1.4 g, 37 mmol) was slowly added thereto under stirring under cooling with ice. After the completion of foaming, the solvent was distilled off under reduced pressure. Water was added to the residue, which was made acidic with 3N hydrochloric acid and washed with ether. The cistern was made basic with aqueous ammonia and then subjected to extraction with dichloromethane. The dichloromethane layer was washed with water and then a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resultant crystals were washed with isopropyl ether to obtain 6.56 g of α-[[(2,3-dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol.

Workup

  1. temperatureunder reflux for 30 minutes
  2. stirringunder stirring
  3. temperatureunder cooling with ice
  4. distillationAfter the completion of foaming, the solvent was distilled off under reduced pressure
  5. additionWater was added to the residue, which
  6. washwashed with ether
  7. extractionsubjected to extraction with dichloromethane
  8. washThe dichloromethane layer was washed with water
  9. dry with materiala saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. washthe resultant crystals were washed with isopropyl ether

Sources & evidence

ORD record
ord-2b0affc108d848d6befc48b531f755e8
Source dataset
uspto-grants-1994_03
Patent number
US05292521

Reaction notes

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